Aprotic diazotization in the presence of cuprous cyanide

In a procedure of extreme simplicity and rapidity a mixture of an aromatic primary amine, copper (I) cyanide and an alkyl nitrite in dimethyl sulphoxide yielded fair to moderate yields of the corresponding nitriles. Side processes observed were reduction (NH2 --> H), nitration (NH2 --> NO2) and hydroxylation (NH2 --> OH). In the case of polyhaloanilines halogen dance products could be detected.